Studies on cardiotonic agents. III. Synthesis of 1-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-3-substituted 2-imidazolidinone and 2-imidazolidinethione derivatives.
A series of 1-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-3-substituted 2-imidazolidinone and 2-imidazolidinethione derivatives was synthesized and examined for cardiotonic activity in anesthetized dogs. Alkylation of the 2-imidazolidinone (1) afforded the N-alkylated products, while alkylation of the 2-imidazolidinethione (12) afforded the S-alkylated derivatives accompanied with a small quantity of the N-alkylated products. The N-alkylated derivatives showed generally potent activity, and the S-alkylated ones exhibited weak activity. Insertion of an alkyl group between the piperidine and the imidazolidinone moiety generally resulted in a fall in activity.
Nomoto
Y
Y
Tokyo Research Laboratory, Kyowa Hakko Kogyo Co., Ltd, Japan.
Obase
H
H
Takai
H
H
Hirata
T
T
Teranishi
M
M
Nakamura
J
J
Ohno
T
T
Kubo
K
K
D000818:Animals; D002316:Cardiotonic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004285:Dogs; D005260:Female; D007093:Imidazoles / Q000138:chemical synthesis / Q000494:pharmacology; D008297:Male; D010880:Piperidines / Q000138:chemical synthesis / Q000494:pharmacology; D011799:Quinazolines / Q000138:chemical synthesis / Q000494:pharmacology; D013871:Thiones / Q000138:chemical synthesis* / Q000494:pharmacology
D002316:Cardiotonic Agents; D007093:Imidazoles; D010880:Piperidines; D011799:Quinazolines; D013871:Thiones